Hunter S. Thompson wasn’t the only eccentric local that led Aspen down a road of debauchery, but he was one that made headlines (and wrote them). As the people of Aspen nearly voted him in as Sheriff, the influx of wealth and fame continued to shake up this one-of-a-kind enclave in the heart of the Rockies. The weird and wild inhabitants shared drinks with celebrities and politicians, turning the town into somewhat of a legend for many.